Substrate control in the asymmetric aminohydroxylation of monosubstituted alkenes: The enantioselective synthesis of GABOB and homoserine derivatives

Synlett

Volumn , Issue 18, 2005, Pages 2829-2831

  Harding, Michael ^a   Bodkin, Jennifer A ^a   Hutton, Craig A ^b,c   McLeod, Malcolm D ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

^c UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Amino acids; Asymmetric aminohydroxylation; Asymmetric catalysis; Regioselectivity

Indexed keywords

4 AMINO 3 HYDROXYBUTYRIC ACID; ALKENE DERIVATIVE; ETHER DERIVATIVE; HOMOSERINE;

AMINOHYDROXYLATION; ARTICLE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; SUBSTITUTION REACTION;

EID: 27844603316     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918939     Document Type: Article

References (42)

1. (a) Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1 2002, 2733.
2. (b) Nilov, D.; Reiser, O. Adv. Synth. Catal. 2002, 344, 1169.
3. (c) O'Brien, P. Angew. Chem. Int. Ed. 1999, 38, 326.
4. (d) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis, Vol. 2; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998, 243.
5. Li, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
6. (a) Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.
7. (b) O'Brien, P.; Osbourne, S. A.; Parker, D. D. J. Chem. Soc., Perkin Trans. 1 1998, 2519.
8. (c) O'Brien, P.; Osborne, S. A.; Parker, D. D. Tetrahedron Lett. 1998, 39, 4099.
9. (a) Bushby, M. L.; Haukaas, M. H.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2984.
10. (b) Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2001, 3, 3899.
11. (c) Demko, Z. P.; Bartsch, M.; Sharpless, K. B. Org. Lett. 2000, 2, 2221.
12. (d) Yang, C.-G.; Wang, J.; Tang, X.-X.; Jiang, B. Tetrahedron: Asymmetry 2002, 13, 383.
13. (e) Feldman, K. S.; Saunders, J. C.; Wrobleski, M. L. J. Org. Chem. 2002, 67, 7096.
14. Davey, R. M.; Brimble, M. A.; McLeod, M. D. Tetrahedron Lett. 2000, 47, 5141.
15. (a) Han, H.; Cho, C.-W.; Janda, K. D. Chem. Eur. J. 1999, 5, 1565.
16. (b) Morgan, A. J.; Masse, C. E.; Panek, J. S. Org. Lett. 1999, 1, 1949.
17. (c) Chuang, C.-Y.; Vassar, V. C.; Ma, Z.; Geney, R.; Ojima, I. Chirality 2002, 14, 151.
18. (a) Zhu, J.; Ma, D. Angew. Chem. Int. Ed. 2003, 42, 5348.
19. (b) Qureshi, A.; Colin, P. L.; Faulkner, D. J. Tetrahedron 2000, 56, 3679.
20. (c) Sasaki, S.; Hamada, Y.; Shiori, T. Synlett 1999, 453.
21. (d) Schmidt, E. W.; Faulkner, D. J. Tetrahedron 1998, 54, 3043.
22. (e) Bewley, C. A.; Debitus, C.; Faulkner, D. J. J. Am. Chem. Soc. 1994, 116, 7631.
23. (a) Otsuka, M.; Obata, K.; Miyata, Y.; Taneka, Y. J. Neurochem. 1971, 18, 287.
24. (b) Buscanino, G. A.; Ferrari, E. Acta Neurol. Scand. 1961, 16, 748.
25. For recent stereospecific syntheses, see: (a) Tiecco, M.; Testaferri, L.; Temperini, A.; Terlizzi, R.; Bagnoli, L.; Marini, F.; Santi, C. Synthesis 2005, 579.
26. (b) Lohray, B. B.; Reddy, A. S.; Bhushan, V. Tetrahedron: Asymmetry 1996, 7, 2411.
27. (c) Misiti, D.; Zappia, G.; Delle Monache, G. Gazz. Chim. Ital. 1995, 125, 219.
28. (d) Misiti, D.; Zappia, G. Synth. Commun. 1995, 25, 2285.
29. For recent enantioselective syntheses, see: (a) Du, Z.; Chen, Z.; Chen, Z.; Yu, X.; Hu, W. Chirality 2004, 16, 516.
30. (b) Sakagami, H.; Kamikubo, T.; Ogasawara, K. Synlett 1997, 221.
31. (c) Puertas, S.; Rebolledo, F.; Gotor, V. J. Org. Chem. 1996, 61, 6024.
32. (d) Kolb, H. C.; Bennani, Y. L.; Sharpless, K. B. Tetrahedron: Asymmetry 1993, 4, 133.
33. The aromatic ethers were prepared from the corresponding phenol and but-3-en-1-ol under Mitsunobu conditions in 75-99% yield. See: Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547.
34. Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507.
35. 1H NMR spectrum of the crude reaction mixture.
36. R = 46.6 min, 96% ee.
37. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
38. 2Ph) was confirmed by the formation of R- and S-Mosher's esters and application of the modified Mosher's method. See: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakaisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
39. Reddy, K. L.; Dress, K. R.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 3667.
40. Fukase, K.; Yasukochi, T.; Nakai, Y.; Kusumoto, S. Tetrahedron Lett. 1996, 37, 3343.
41. Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564.
42. 2]}, synthesised in two steps from (S)-glutamic acid.